Check out the instructions/suggestions here.
Music from iPod to computer (using option 2).
There's also another method. I've successfully tested this across several different Windows PCs.
Open iTunes and select edit/preferences/advanced/general. Put a check mark in the box marked "copy files to iTunes music folder when adding to library" and also "keep iTunes music folder organized", then click 'ok'.
Connect the iPod whilst holding down the shift/ctrl keys to prevent any auto sync, and if you see the dialogue window asking if you want to sync to this itunes library, click
'no'.
Then go to file/add folder, open 'my computer', select your iPod and click 'ok'.
The music files should transfer to your iTunes.
If this doesn't work (and it may not because officially it's not supposed to), there's
Yamipod. This is a free program that transfers music and playlists etc from iPod back to the computer. However, it does not transfer playcounts/ratings etc.
The above methods may depend on what version of iTunes you are running.
If none of these methods work, try
CopyPod.
If you are using iTunes version 7 or later, then you can transfer purchased iTunes store music from the iPod to an authorized computer by using the "file/transfer purchases from iPod" menu. Note that the maximum of 5 authorized computers applies here.
